Search Winter Park Cottage Rentals from CA $242
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Winter Park cottages
Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Pool Days & Hammock Naps Book Your Escape Before It’s GoneLake Mary
9.8 out of 10, Exceptional, (59 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
Mike B.
The price is CA $152
CA $372 total
includes taxes & fees
Jul 6 - Jul 7
Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Last-Minute July 4th Getaway! Charming Cottage • Early Check-InLake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
Tricia S.
The price is CA $128
CA $338 total
includes taxes & fees
Jun 29 - Jun 30
Downtown Cottage
Downtown CottageColonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
Jerred B.
The price is CA $83
CA $242 total
includes taxes & fees
Jul 1 - Jul 2
Newly Remodeled Tiny Home 20 minutes from Disney!~
Newly Remodeled Tiny Home 20 minutes from Disney!~Kissimmee
The price is CA $121
CA $300 total
includes taxes & fees
Jun 29 - Jun 30
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Shore Steps Cottage - Walking Distance To The Town Of WindermereWindermere
The price is CA $212
CA $539 total
includes taxes & fees
Jun 29 - Jun 30
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Romantic Lakefront Getaway with Balcony near Downtown OrlandoOrlando
The price is CA $139
CA $321 total
includes taxes & fees
Jun 29 - Jun 30
Fire Pit & Yard: Updated Winter Garden Home!
Fire Pit & Yard: Updated Winter Garden Home!Winter Garden
The price is CA $344
CA $777 total
includes taxes & fees
Jun 30 - Jul 1
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!College Park
10.0 out of 10, Exceptional, (41 reviews)
"Our hosts were incredibly accommodating and welcoming. This was the perfect place for us to stay while in town for a wedding in Winter Park. Thank you! "
Danielle S.
The price is CA $241
CA $490 total
includes taxes & fees
Jul 13 - Jul 14
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find vacation rentals that suit your style
Aparthotels
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Winter Park Hotel Reviews
Coco Key Hotel & Water Park Resort
10/10 Excellent
Find out more about Winter Park
Winter Park Cottages information
Number of reviews | 119 |
|---|---|
Accommodation | 355 Cottages |
Lowest Price | CA $242 |
Highest Price | CA $1,305 |
Frequently asked questions
Explore a world of travel with Expedia
- Cabin Rentals in Maitland
- Adults Only Resorts & in Orlando
- 777bd
- All Inclusive Resorts and in Orlando
- Family Hotels in Orlando
- Kissimmee Hotels
- Motels in Orlando
- Townhomes in Orlando
- Vacation Homes in Orlando
- B&B in Longwood
- Condo Rentals in Orlando
- Cottages in Orlando
- Houseboats in Orlando
- Cruise Ships in Orlando
- Drury Plaza Hotel Orlando
- Cabin Rentals in Orlando
- Condo Resorts in Orlando
- Aparthotels in Orlando
- Hotels near Orange County Convention Center
- B&B in Maitland
- Hotels near Walt Disney World® Resort
- Walt Disney World Resort in Orlando
- Hotels with Free Airport Shuttle in Orlando
- Guest Houses in Altamonte Springs
- 5 Star Hotels in Orlando
- Apartments in Orlando
- Hotels with a Lazy River in Orlando
- Hilton Vacation Club Mystic Dunes Orlando
- Waterpark Hotels in Orlando
- Condo Rentals in Winter Park
- Orlando Hotels
- Hostels in Orlando
- Universal Orlando Resort in Orlando
- Guest Houses in Fern Park
- B&B in Orlando
- Resorts in Orlando
- Resorts in North Orlando
- Rv Parks in Orlando
- Motels in Fern Park
- Cheap Hotels in Orlando
- Hotels near Orlando Intl.
- Villas in Orlando
- Hostels in Casselberry
- Hotels near Universal Studios Florida
- Lodges in Orlando
- Cabin Rentals in Northeast Orlando
- All Inclusive Resorts and in Florida
- Houseboats in Fern Park
- Guest Houses in Orlando
- Farmstay in Orlando
- Flights from Orlando Intl.
- Flights from Toronto (YYZ) to Orlando (MCO)
- Flights from Kitchener (YKF) to Orlando (MCO)
- Flights from Regina (YQR) to Orlando (MCO)
- Flights from Orlando Sanford Intl.
- Flights from Buffalo (BUF) to Orlando (MCO)
- Flights from Fort Lauderdale (FLL) to Orlando (MCO)
- Flights from Vancouver (YVR) to Orlando (MCO)
- Flights from Ogdensburg (OGS) to Orlando (MCO)
- Flights from Miami (MIA) to Orlando (MCO)
- Flights from Calgary (YYC) to Orlando (MCO)
- Flights from Toronto (YYZ) to Orlando (ORL)
- Flights from Edmonton (YEG) to Orlando (MCO)
- Flights from Syracuse (SYR) to Orlando (MCO)
- Flights from London (YXU) to Orlando (MCO)
- Flights from Detroit (DTW) to Orlando (MCO)
- Flights from Halifax (YHZ) to Orlando (MCO)
- Flights from Saskatoon (YXE) to Orlando (MCO)
- Flights from Hamilton (YHM) to Orlando (MCO)
- Flights from Montreal (YUL) to Orlando (MCO)
- Flights to Orlando
- Flights from New York (JFK) to Orlando (MCO)
- Flights from Seattle (SEA) to Orlando (MCO)
- Flights from Ottawa (YOW) to Orlando (MCO)
- Flights from Windsor (YQG) to Orlando (MCO)
- Flights from Moncton (YQM) to Orlando (MCO)
- Flights from Plattsburgh (PBG) to Orlando (MCO)
- Flights from Winnipeg (YWG) to Orlando (MCO)
- Flights to Florida
- Flights from St. John's (YYT) to Orlando (MCO)
- Flights from Bangor (BGR) to Orlando (MCO)
- Disney's Hollywood Studios®
- All inclusive Vacation Packages Florida
- Universal Studios Florida
- Universal Orlando Resort
- Universal’s Volcano Bay
- Walt Disney World® Resort
- Florida Vacations
- Orlando Vacations
- The Wizarding World of Harry PotterTM
- Orlando International Premium Outlets
- All inclusive Vacation Packages Orlando